Polycyclic compound and organic light-emitting device using the same

Abstract

To provide a polycyclic compound which can be employed in various organic layers provided in an organic light-emitting device, and to provide a high-efficiency and long-life organic light-emitting device having remarkably improved light-emitting efficiency and life characteristics by including the same.SOLUTION: The organic light-emitting compound is represented by formula A-1 or formula A-2.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a polycyclic compound and an organic light-emitting device using the same, which has a high efficiency and a long life and exhibits significantly improved life characteristics and luminous efficiency. [Background technology]

[0002] An organic light-emitting device is a self-emitting device in which electrons injected from an electron injection electrode (cathode electrode) and holes injected from a hole injection electrode (anode electrode) combine in the light-emitting layer to form excitons, which then emit light by releasing energy. Such organic light-emitting devices are attracting attention as next-generation light sources due to their advantages of low driving voltage, high brightness, wide viewing angle, and fast response speed, as well as their applicability to full-color flat panel light-emitting displays.

[0003] In order for such an organic light emitting device to exhibit the above-mentioned characteristics, it is necessary to optimize the structure of the organic layers in the device and ensure that the materials constituting each organic layer, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, and an electron blocking material, are supported by stable and efficient materials. However, there is still a need to continue developing stable and efficient organic layer structures and materials for organic light emitting devices.

[0004] As described above, there is a continuing demand for the development of element structures that can improve the light-emitting properties of organic light-emitting elements, as well as new materials that support such structures. Summary of the Invention [Problem to be solved by the invention]

[0005] Therefore, the present invention provides a compound that can be used in an organic layer of a device to realize a device having high efficiency and long life characteristics, and an organic light emitting device including the compound. [Means for solving the problem]

[0006] In order to solve the above problems, the present invention provides a polycyclic compound represented by the following chemical formula A-1 or chemical formula A-2, characterized in that a structure represented by the following structural formula 1 is introduced and contained therein.

[0007] JPEG2026009958000001.jpg51100 [Structural formula 1] JPEG2026009958000002.jpg2951

[0008] The structures of the chemical formula A-1, chemical formula A-2 and structural formula 1, and specific compounds realized thereby, and the rings Q1 to Q3, X, Y1 to Y3 and R 11 ~R 18 The definition will be explained later.

[0009] The present invention also provides an organic light-emitting device comprising a first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more specific polycyclic compounds represented by Chemical Formula A-1 or Chemical Formula A-2. [Effects of the Invention]

[0010] By employing the polycyclic compound according to the present invention in an organic layer in a device, an organic light-emitting device with high efficiency and long life can be realized. DETAILED DESCRIPTION OF THE INVENTION

[0011] The present invention will now be described in further detail.

[0012] The present invention relates to a polycyclic compound included in an organic light-emitting device, which is represented by the following chemical formula A-1 or A-2, and which is characterized by incorporating a dibenzofuran or dibenzothiophene derivative represented by the following structural formula 1, thereby realizing a highly efficient organic light-emitting device.

[0013] JPEG2026009958000003.jpg55101

[0014] In the chemical formula A-1 and chemical formula A-2, Q1 to Q3 are the same or different and are each independently selected from a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aromatic heterocycle having 2 to 50 carbon atoms, a substituted or unsubstituted polycyclic non-aromatic fused hydrocarbon ring having 6 to 50 carbon atoms, and a substituted or unsubstituted polycyclic non-aromatic fused heterocycle having 2 to 50 carbon atoms.

[0015] Y1 to Y3 are the same or different and each independently represent one selected from N—R1, CR2R3, O, S, Se, and SiR4R5.

[0016] R1 to R5 are the same or different and each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 5 ... It is any one selected from an unsubstituted polycyclic non-aromatic fused hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted polycyclic non-aromatic fused heterocycle having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a nitro group, a cyano group, and a halogen group.

[0017] Furthermore, each of R1 to R5 can be bonded to any one of the Q1 to Q3 rings to further form an alicyclic or aromatic monocyclic or polycyclic ring.

[0018] In addition, R2 and R3, and R4 and R5, respectively, can be linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring.

[0019] In addition, at least one of Y2 and Y3 is N-R6, and R6 is represented by the following structural formula 1. The compound represented by chemical formula A-1 or chemical formula A-2 according to the present invention is characterized in that it contains at least one or more dibenzofuran or dibenzothiophene derivatives introduced at specific positions.

[0020] [Structural formula 1] JPEG2026009958000004.jpg2951

[0021] In the structural formula 1, X is O or S; R 11 ~R 18are the same or different and each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted polycyclic non-aromatic fused hydrocarbon ring having 6 to 50 carbon atoms, a substituted Or it is any one selected from an unsubstituted polycyclic non-aromatic fused heterocycle having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, a substituted or unsubstituted aluminum group, a phosphoryl group, a hydroxy group, a selenium group, a tellurium group, a nitro group, a cyano group, and a halogen group.

[0022] R 11 ~R 18 Any one of the R 11 ~R 18 may be linked to each other or to adjacent substituents to form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring may be substituted with one or more heteroatoms selected from N, S, and O.

[0023] As described above, the characteristic structure of Chemical Formula A-1 or Chemical Formula A-2 according to the present invention and the ring-forming structure realized by the definition of the substituents can be confirmed from the specific compounds described below.

[0024] According to one embodiment of the present invention, the compound of formula A-1 or A-2 may be represented by any one of the following formulas A-3 and A-4:

[0025] JPEG2026009958000005.jpg5296

[0026] In the chemical formula A-3 and chemical formula A-4, Z is CR or N.

[0027] The R is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted polycyclic non-aromatic fused hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted polycyclic non-aromatic fused hydrocarbon ring having 2 ... Z and R are any one selected from the group consisting of a fused aromatic heterocycle, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, a substituted or unsubstituted aluminum group, a phosphoryl group, a hydroxy group, a selenium group, a tellurium group, a nitro group, a cyano group, and a halogen group, and the multiple Zs and Rs are the same or different.

[0028] The plurality of Rs may be bonded to each other or to adjacent substituents to form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring may be substituted with any one or more heteroatoms selected from N, S, and O.

[0029] Y1 to Y3 are defined the same as in Chemical Formula A-1 and Chemical Formula A-2.

[0030] On the other hand, in the present invention, the term "substituted or unsubstituted" refers to the Q1 to Q3 rings, R1 to R6, R 11 ~R 18 and the like are each substituted with one or more substituents selected from the group consisting of deuterium, cyano group, halogen group, hydroxy group, nitro group, amino group, alkyl group, cycloalkyl group, halogenated alkyl group, alkenyl group, alkynyl group, heteroalkyl group, heterocycloalkyl group, aryl group, arylalkyl group, heteroaryl group, heteroarylalkyl group, alkoxy group, alkylamine group, arylamine group, heteroarylamine group, alkylsilyl group, arylsilyl group, and aryloxy group, or are substituted with a substituent in which two or more of the above substituents are linked, or have no substituents at all.

[0031] Furthermore, the range of the carbon number of the alkyl group or aryl group in the "substituted or unsubstituted alkyl group having 1 to 30 carbon atoms," "substituted or unsubstituted aryl group having 6 to 50 carbon atoms," etc. means the total number of carbon atoms constituting the alkyl moiety or aryl moiety when considered as unsubstituted without taking into account the portion substituted with the substituent. For example, a phenyl group substituted with a butyl group at the para position corresponds to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.

[0032] In addition, in the present invention, the term "bonding with adjacent groups to form a ring" means that adjacent groups can bond to form a substituted or unsubstituted alicyclic or aromatic ring, and "adjacent substituents" may refer to a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at the ortho positions on a benzene ring and two substituents substituted on the same carbon atom on an aliphatic ring may be interpreted as "adjacent substituents" to each other.

[0033] In the present invention, the alkyl group may be a straight chain or a branched chain, and specific examples thereof include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethyl Examples of alkyl groups include, but are not limited to, butyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

[0034] In the present invention, alkenyl groups include straight-chain or branched-chain alkenyl groups, and may be further substituted with other substituents. Specific examples include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl, and styrenyl groups.

[0035] In the present invention, alkynyl groups also include straight or branched chains and may be further substituted with other substituents, including, but not limited to, ethynyl, 2-propynyl, and the like.

[0036] In the present invention, the aromatic hydrocarbon ring or aryl group may be monocyclic or polycyclic. Examples of monocyclic aryl groups include a phenyl group, a biphenyl group, a terphenyl group, and a stilbene group. Examples of polycyclic aryl groups include a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a tetracenyl group, a chrysenyl group, a fluorenyl group, an acenaphthacenyl group, a triphenylene group, and a fluoranthene group. However, the scope of the present invention is not limited to these examples.

[0037] In the present invention, the aromatic heterocycle or heteroaryl group is an aromatic ring containing one or more heteroatoms, and examples thereof include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, a triazole group, an acridyl group, a pyridazine group, a pyrazinyl group, a quinolinyl group, a quinazoline group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, Examples of such groups include, but are not limited to, pyridopyrazinyl groups, pyrazinopyrazinyl groups, isoquinoline groups, indole groups, carbazole groups, benzoxazole groups, benzimidazole groups, benzothiazole groups, benzocarbazole groups, benzothiophene groups, dibenzothiophene groups, benzofuranyl groups, dibenzofuranyl groups, phenanthroline groups, thiazolyl groups, isoxazolyl groups, oxadiazolyl groups, thiadiazolyl groups, benzothiazolyl groups, and phenothiazinyl groups.

[0038] In the present invention, an aliphatic hydrocarbon ring refers to a non-aromatic ring consisting only of carbon and hydrogen atoms, examples of which include a monocycle or a polycycle, which may be further substituted with other substituents. A polycycle refers to a group directly linked to or fused with another ring group. The other ring group may be an aliphatic hydrocarbon ring, but may also be other types of ring groups, such as an aliphatic heterocycle, an aryl group, or a heteroaryl group. Specific examples include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, adamantyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl; cycloalkanes such as cyclohexane and cyclopentane; and cycloalkenes such as cyclohexene and cyclobutene, but are not limited thereto.

[0039] In the present invention, the term "aliphatic heterocycle" refers to an aliphatic ring containing one or more heteroatoms, such as O, S, Se, N, or Si, and may also include a monocycle or polycycle, which may be further substituted with other substituents. The term "polycycle" refers to a group in which a heterocycloalkyl, heterocycloalkane, heterocycloalkene, or the like is directly linked to or fused with another ring group, and the other ring group may be an aliphatic heterocycle, or may be another type of ring group, such as an aliphatic hydrocarbon ring, an aryl group, or a heteroaryl group.

[0040] In the present invention, a polycyclic non-aromatic fused hydrocarbon ring means a ring in which two or more rings are fused to each other and the entire molecule has non-aromaticity, and a polycyclic non-aromatic fused heterocycle means a fused non-aromatic hydrocarbon ring containing a heteroatom selected from N, O, P, and S in addition to C, and examples thereof include, but are not limited to, compounds having the following structures:

[0041] JPEG2026009958000006.jpg22127

[0042] In the present invention, the alkoxy group may specifically be methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, etc., but is not limited to these.

[0043] In the present invention, the silyl group may be -SiH, an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, an arylheteroarylsilyl group, or the like, and specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, and dimethylfurylsilyl.

[0044] In the present invention, the amine group may be -NH, an alkylamine group, an arylamine group, an arylheteroarylamine group, etc., where the arylamine group refers to an amine substituted with an aryl group, the alkylamine group refers to an amine substituted with an alkyl group, and the arylheteroarylamine group refers to an amine substituted with an aryl and a heteroaryl group. Examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl and heteroaryl groups in the arylamine group and arylheteroarylamine group may be a monocyclic aryl group, a monocyclic heteroaryl group, or a polycyclic aryl group or a polycyclic heteroaryl group. The arylamine group and arylheteroarylamine group containing two or more aryl groups and two or more heteroaryl groups may contain a monocyclic aryl group (heteroaryl group), a polycyclic aryl group (heteroaryl group), or both a monocyclic aryl group (heteroaryl group) and a polycyclic aryl group (heteroaryl group). The aryl group and heteroaryl group in the arylamine group and arylheteroarylamine group may be selected from the examples of the aryl group and heteroaryl group given above.

[0045] In the present invention, the aryl group in the aryloxy group and the arylthioxy group is the same as the above-mentioned exemplary aryl group. Specific examples of the aryloxy group include phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group, 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, and 9-phenanthryloxy group. Examples of the arylthioxy group include, but are not limited to, phenylthioxy group, 2-methylphenylthioxy group, and 4-tert-butylphenylthioxy group.

[0046] In the present invention, examples of halogen groups include fluorine, chlorine, bromine or iodine.

[0047] More specifically, the polycyclic aromatic derivative compound represented by chemical formula A-1 or chemical formula A-2 according to the present invention may be any one selected from the following compounds, through which specific substituents can be clearly identified, but the scope of chemical formula A-1 or chemical formula A-2 according to the present invention is not limited thereby.

[0048] JPEG2026009958000007.jpg187150 JPEG2026009958000008.jpg185150 JPEG2026009958000009.jpg179150 JPEG2026009958000010.jpg192150 JPEG2026009958000011.jpg165150 JPEG2026009958000012.jpg156150 JPEG2026009958000013.jpg188150 JPEG2026009958000014.jpg186150 JPEG2026009958000015.jpg180150 JPEG2026009958000016.jpg187150 JPEG2026009958000017.jpg189150 JPEG2026009958000018.jpg164150 JPEG2026009958000019.jpg169150

[0049] As can be seen from the above specific compounds, according to the present invention, a polycyclic structure containing boron (B) can be formed, and a characteristic substituent, including a substituent represented by Structural Formula 1, can be introduced into the polycyclic structure to synthesize an organic light-emitting material having the unique properties of the substituent. For example, by introducing into the structure a substituent used in materials for the hole injection layer, hole transport layer, light-emitting layer, electron transport layer, electron injection layer, electron blocking layer, and hole blocking layer used in the manufacture of organic light-emitting devices, a material satisfying the requirements for each organic layer, preferably a material used in the light-emitting layer, can be prepared. This allows for the realization of a highly efficient organic light-emitting device.

[0050] Another aspect of the present invention relates to an organic light-emitting device comprising a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer may contain at least one organic light-emitting compound according to the present invention represented by Chemical Formula A-1 or Chemical Formula A-2.

[0051] That is, the organic light emitting device according to an embodiment of the present invention may have a structure including a first electrode, a second electrode, and an organic layer disposed therebetween, and may be manufactured using a conventional device manufacturing method and materials in the art, except that the organic light emitting compound of Chemical Formula A-1 or Chemical Formula A-2 according to the present invention is used in the organic layer of the device.

[0052] The organic layer of the organic light-emitting device according to the present invention may have a single-layer structure or a multi-layer structure in which two or more organic layers are stacked. For example, the organic layer may have a structure including a hole injection layer, a hole transport layer, a hole blocking layer, an emitting layer, an electron blocking layer, an electron transport layer, an electron injection layer, etc. However, the organic layer is not limited thereto, and may include fewer or more organic layers. The structure of the organic layer of the preferred organic light-emitting device according to the present invention will be described in more detail in the examples below.

[0053] The organic light emitting device according to the present invention includes an anode, a hole transport layer, an emitting layer, an electron transport layer, and a cathode, and may further include a hole injection layer between the anode and the hole transport layer, or an electron injection layer between the electron transport layer and the cathode, if necessary. In addition, one or two intermediate layers may be further formed, and a hole blocking layer or an electron blocking layer may also be further formed.

[0054] According to one embodiment of the present invention, the organic layer interposed between the first electrode and the second electrode includes an emitting layer, and the emitting layer comprises a host and a dopant, and the compound represented by Chemical Formula A-1 or Chemical Formula A-2 according to the present invention may be included as a dopant in the emitting layer.

[0055] In this case, the content of the dopant in the light-emitting layer may be selected from the range of about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

[0056] According to an embodiment of the present invention, the host may be an anthracene compound represented by the following formula B:

[0057] [ka]

[0058] In the above chemical formula B, R 21 ~R 28are the same or different and each independently represent one selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted polycyclic non-aromatic fused heterocycle having 2 to 50 carbon atoms, a nitro group, a cyano group, and a halogen group.

[0059] Ar1 and Ar3 are the same or different and each independently represent a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms.

[0060] Ar2 and Ar4 are the same or different and each independently represent one selected from hydrogen, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a substituted or unsubstituted polycyclic non-aromatic fused heterocycle having 2 to 50 carbon atoms.

[0061] D n means that hydrogen atoms of Ar1 to Ar4 in chemical formula B have been substituted with deuterium atoms, and n is an integer of 0 to 30.

[0062] The anthracene host derivative compound represented by the chemical formula B according to the present invention may be any one selected from the following compounds, but the scope of the chemical formula B according to the present invention is not limited thereto.

[0063] JPEG2026009958000021.jpg175150 JPEG2026009958000022.jpg192150 JPEG2026009958000023.jpg178150 JPEG2026009958000024.jpg184150 JPEG2026009958000025.jpg198150 JPEG2026009958000026.jpg202150 JPEG2026009958000027.jpg183150 JPEG2026009958000028.jpg193150 JPEG2026009958000029.jpg162150 JPEG2026009958000030.jpg155150 JPEG2026009958000031.jpg167150 JPEG2026009958000032.jpg171150 JPEG2026009958000033.jpg204150 JPEG2026009958000034.jpg171150 JPEG2026009958000035.jpg209150 JPEG2026009958000036.jpg172150 JPEG2026009958000037.jpg165150 JPEG2026009958000038.jpg191150 JPEG2026009958000039.jpg195150 JPEG2026009958000040.jpg165150 JPEG2026009958000041.jpg174150 JPEG2026009958000042.jpg140150

[0064] Furthermore, according to one embodiment of the present invention, the light-emitting layer containing the compound represented by Chemical Formula A-1 or Chemical Formula A-2 may have a maximum peak wavelength of EL (electroluminescence) of 454 nm or less, preferably 440 nm to 454 nm.

[0065] The electroluminescence (EL) spectrum is calculated as the product of the photoluminescence (PL) spectrum, which reflects the inherent properties of the host compound or dopant compound contained in the light-emitting layer, and the outcoupling emittance spectrum, which is determined by the structure and optical properties of the organic light-emitting device including other organic layers such as an electron transport layer. The peak wavelength refers to the wavelength at which the peak intensity is greatest among the peak wavelengths of the PL, EL, etc. spectra.

[0066] The light-emitting layer including the compound represented by Chemical Formula A-1 or Chemical Formula A-2 according to an embodiment of the present invention has a maximum EL peak wavelength of 454 nm or less, thereby realizing deep blue light emission.

[0067] The organic light emitting device according to the present invention may include a plurality of blue light emitting layers having different wavelength bands in addition to the blue light emitting layer, and may further include a red light emitting layer, a green light emitting layer, a yellow light emitting layer, etc.

[0068] Furthermore, when the compound according to the present invention is employed in the blue light-emitting layer of a quantum dot organic light-emitting device having not only a light-emitting phosphor layer but also a quantum dot layer formed on the light-emitting surface, it is possible to realize an organic light-emitting device that emits deep blue light with high efficiency.

[0069] Meanwhile, the specific structure of the organic light emitting device according to an embodiment of the present invention, the manufacturing method thereof, and the materials of each organic layer will be described as follows.

[0070] First, an anode is formed by coating a substrate with an anode material. The substrate can be a substrate commonly used in organic light-emitting devices, but an organic substrate or transparent plastic substrate is preferred because of its transparency, surface smoothness, ease of handling, and water resistance. The anode material can be transparent and highly conductive, such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO), or zinc oxide (ZnO).

[0071] A hole injection layer is formed on the anode electrode by vacuum thermal deposition or spin coating of a hole injection layer material, and then a hole transport layer is formed on the hole injection layer by vacuum thermal deposition or spin coating of a hole transport layer material.

[0072] The material for the hole injection layer is not particularly limited as long as it is a material commonly used in the art. Specific examples thereof include 2-TNATA [4,4',4''-tris(2-naphthylphenyl-phenylamino)-triphenylamine] (4,4',4''-tris(2-naphthylphenyl-phenylamino)-triphenylamine), NPD [N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine] (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine), TPD [N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'- diamine] (N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine), DNTPD [N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine] (N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), HAT-CN [1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile] (1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile), and the like can be used.

[0073] The material for the hole transport layer is not particularly limited as long as it is a material commonly used in the art, and examples thereof include N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) and N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine (α-NPD).

[0074] Next, a hole-assisting layer and an emitting layer are sequentially stacked on the hole-transporting layer, and a hole-blocking layer can be optionally formed as a thin film on the emitting layer by vacuum deposition or spin coating. The hole-blocking layer prevents the device's lifetime and efficiency from decreasing if holes pass through the organic emitting layer to the cathode. The hole-blocking layer uses a material with a very low HOMO (Highest Occupied Molecular Orbital) level to prevent this problem. The hole-blocking material used is not particularly limited, but should have electron transport capability and a higher ionization potential than the emitting compound. Representative examples include BAlq, BCP, and TPBI.

[0075] The hole blocking layer may be made of, but is not limited to, BAlq, BCP, Bphen, TPBI, NTAZ, BeBq2, OXD-7, Liq, or the like.

[0076] An electron transport layer is deposited on the hole blocking layer by vacuum deposition or spin coating, followed by forming an electron injection layer. A metal for forming a cathode is then vacuum thermally deposited on the electron injection layer to form a cathode electrode, thereby completing an organic light emitting device according to one embodiment of the present invention.

[0077] Here, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. can be used as the metal for forming the cathode, and a transmission type cathode using ITO or IZO can be used to obtain a front light emitting element.

[0078] The electron transport layer may be made of a known electron transport material that stably transports electrons injected from the cathode. Examples of known electron transport materials include quinoline derivatives, particularly tris(8-quinolinolato)aluminum (Alq), TAZ, BAlq, beryllium bis(benzoquinolin-10-olate: Bebq), and oxadiazole derivatives such as PBD, BMD, and BND.

[0079] Each of the organic layers may be formed by a monomolecular deposition method or a solution process, where the deposition method refers to a method of forming a thin film by evaporating a material used to form each layer by heating under vacuum or low pressure, and the solution process refers to a method of mixing a material used to form each layer with a solvent and forming a thin film by inkjet printing, roll-to-roll coating, screen printing, spray coating, dip coating, spin coating, or the like.

[0080] In addition, the organic light emitting device according to the present invention may be used in a flat display device, a flexible display device, a monochrome or white flat lighting device, a monochrome or white flexible lighting device, a vehicle display device, a virtual or augmented reality display device, etc. [Example]

[0081] Synthesis Example 1: Synthesis of [Compound 12] Synthesis Example 1-1: Synthesis of Intermediate A-1 JPEG2026009958000043.jpg23118<Intermediate A-1a><Intermediate A-1b> <Intermediate A-1>

[0082] A reactor was charged with 35 g of <Intermediate A-1a>, 23.9 g of <Intermediate A-1b>, 2.67 g of tris(dibenzylideneacetone)dipalladium(0), 1.82 g of bis(diphenylphosphino)-1,1'-binaphthyl, 28 g of sodium tert-butoxide, and 450 mL of toluene, and the mixture was refluxed and stirred for 3 hours. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was separated. Purification by silica gel chromatography yielded <Intermediate A-1> (40.5 g, 90.1%).

[0083] Synthesis Example 1-2: Synthesis of Intermediate A-2 JPEG2026009958000044.jpg29135<Intermediate A-1> <Intermediate A-2a> <Intermediate A-2>

[0084] 24 g of Intermediate A-1, 24.8 g of Intermediate A-2a, 0.8 g of bis(tri-tert-butylphosphine)palladium(0), 12 g of sodium tert-butoxide, and 350 mL of toluene were added to a reactor and stirred under reflux for 6 hours. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was separated. Purification by silica gel chromatography yielded Intermediate A-2 (35.2 g, 87.5%).

[0085] Synthesis Example 1-3: Synthesis of Intermediate A-3 JPEG2026009958000045.jpg38112<Intermediate A-3a><Intermediate A-3b> <Intermediate A-3>

[0086] 50g of <Intermediate A-3a>, 60.3g of <Intermediate A-3b>, 0.4g of palladium (II) acetate, 25.6g of sodium tert-butoxide, 1g of Xantphos, and 500mL of toluene were added to a reactor, and the mixture was refluxed and stirred for 16 hours. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was separated. Purification by silica gel chromatography yielded <Intermediate A-3> (59.6g, 76.9%).

[0087] Synthesis Example 1-4: Synthesis of Intermediate A-4 JPEG2026009958000046.jpg44127<Intermediate A-3> <Intermediate A-4a> <Intermediate A-4>

[0088] A reactor was charged with 50 g of Intermediate A-3, 23.1 g of Intermediate A-4a, 2.1 g of tris(dibenzylideneacetone)dipalladium(0), 1.43 g of bis(diphenylphosphino)-1,1'-binaphthyl, 22 g of sodium tert-butoxide, and 500 mL of toluene, and the mixture was refluxed and stirred for 16 hours. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was separated. Purification by silica gel chromatography yielded Intermediate A-4 (43.4 g, 70.3%).

[0089] Synthesis Example 1-5: Synthesis of Intermediate A-5 JPEG2026009958000047.jpg40130<Intermediate A-2> <Intermediate A-4> <Intermediate A-5>

[0090] 32 g of <Intermediate A-2>, 34.4 g of <Intermediate A-4>, 0.63 g of bis(tri-tert-butylphosphine)palladium(0), 11.9 g of sodium tert-butoxide, and 300 mL of toluene were added to a reactor, and the mixture was stirred under reflux for 16 hours. After cooling to room temperature, ethyl acetate and water were added, and the organic layer was separated. Purification by silica gel chromatography yielded <Intermediate A-5> (50.5 g, 80%).

[0091] Synthesis Example 1-6: Synthesis of [Compound 12] JPEG2026009958000048.jpg47126<Intermediate A-5> [Compound 12]

[0092] A reactor was charged with 48 g of Intermediate A-5 and 300 mL of tert-butylbenzene, followed by dropwise addition of 83 mL of 1.7 M tert-butyllithium pentane solution at -78°C. The mixture was heated to 60°C and stirred for 2 hours. Afterwards, nitrogen was blown in at 60°C to completely remove the pentane. After cooling to -78°C, 14.1 mL of boron tribromide was added dropwise. The mixture was heated to room temperature and stirred for 2 hours. After cooling to 0°C, 25 mL of N,N-diisopropylethylamine was added dropwise. The mixture was heated to 120°C and stirred for 16 hours. After cooling to room temperature, 10% aqueous sodium acetate and ethyl acetate were added, and the organic layer was separated and concentrated under reduced pressure. Purification by silica gel chromatography yielded [Compound 12] (7.2 g, 15.4%).

[0093] MS (MALDI-TOF): m / z 991.47 [M + ]

[0094] Synthesis Example 2: Synthesis of [Compound 13] Synthesis Example 2-1: Synthesis of Intermediate B-1 JPEG2026009958000049.jpg29118<Intermediate B-1a> <Intermediate B-1b> <Intermediate B-1>

[0095] Intermediate B-1 was obtained in the same manner as in Synthesis Example 1-1, except that Intermediate B-1a was used instead of Intermediate A-1a and Intermediate B-1b was used instead of Intermediate A-1b. (Yield: 76.2%)

[0096] Synthesis Example 2-2: Synthesis of Intermediate B-2 JPEG2026009958000050.jpg34128<Intermediate B-1> <Intermediate B-2a> <Intermediate B-2>

[0097] In the same manner as in Synthesis Example 1-2, Intermediate B-1 was used instead of Intermediate A-1, and Intermediate B-2a was used instead of Intermediate A-2a, to obtain Intermediate B-2 (yield 65.4%).

[0098] Synthesis Example 2-3: Synthesis of Intermediate B-3 JPEG2026009958000051.jpg42130<Intermediate B-2> <Intermediate A-4> <Intermediate B-3>

[0099] Intermediate B-3 was obtained in the same manner as in Synthesis Example 1-5, except that Intermediate B-2 was used instead of Intermediate A-2. (Yield: 93.8%)

[0100] Synthesis Example 2-4: Synthesis of [Compound 13] JPEG2026009958000052.jpg48126<Intermediate B-3> [Compound 13]

[0101] Compound 13 was obtained in the same manner as in Synthesis Example 1-6, except that Intermediate B-3 was used instead of Intermediate A-5. (Yield: 19.7%)

[0102] MS (MALDI-TOF): m / z 977.46 [M + ]

[0103] Synthesis Example 3: Synthesis of [Compound 73] Synthesis Example 3-1: Synthesis of Intermediate C-1 JPEG2026009958000053.jpg20118<Intermediate C-1a><Intermediate A-1b> <Intermediate C-1>

[0104] Intermediate C-1 was obtained in the same manner as in Synthesis Example 1-1, except that Intermediate C-1a was used instead of Intermediate A-1a. (Yield: 72.1%)

[0105] Synthesis Example 3-2: Synthesis of Intermediate C-2 JPEG2026009958000054.jpg27130<Intermediate C-1><Intermediate B-2a> <Intermediate C-2>

[0106] Intermediate C-2 was obtained in the same manner as in Synthesis Example 2-2, except that Intermediate C-1 was used instead of Intermediate B-1 (yield 78.3%).

[0107] Synthesis Example 3-3: Synthesis of Intermediate C-3 JPEG2026009958000055.jpg24125<Intermediate C-3a><Intermediate A-1b> <Intermediate C-3>

[0108] Intermediate C-3 was obtained in the same manner as in Synthesis Example 1-1, except that Intermediate C-3a was used instead of Intermediate A-1a (yield: 85.1%).

[0109] Synthesis Example 3-4: Synthesis of Intermediate C-4 JPEG2026009958000056.jpg28132<Intermediate C-3> <Intermediate A-3b> <Intermediate C-4>

[0110] Intermediate C-4 was obtained in the same manner as in Synthesis Example 1-3, except that Intermediate C-3 was used instead of Intermediate A-3a (yield: 46.2%).

[0111] Synthesis Example 3-5: Synthesis of Intermediate C-5 JPEG2026009958000057.jpg42128<Intermediate C-4> <Intermediate A-4a> <Intermediate C-5>

[0112] Intermediate C-5 was obtained in the same manner as in Synthesis Example 1-4, except that Intermediate C-4 was used instead of Intermediate A-3. (Yield: 90.4%)

[0113] Synthesis Example 3-6: Synthesis of Intermediate C-6 JPEG2026009958000058.jpg35130<Intermediate C-2> <Intermediate C-5> <Intermediate C-6>

[0114] Intermediate C-6 was obtained in the same manner as in Synthesis Example 1-5, except that Intermediate C-2 was used instead of Intermediate A-2 and Intermediate C-5 was used instead of Intermediate A-4. (Yield: 81.6%)

[0115] Synthesis Example 3-7: Synthesis of [Compound 73] JPEG2026009958000059.jpg41125<Intermediate C-6> [Compound 73]

[0116] Compound 73 was obtained in the same manner as in Synthesis Example 1-6, except that Intermediate C-6 was used instead of Intermediate A-5. (Yield: 14.4%)

[0117] MS (MALDI-TOF): m / z 977.46 [M + ]

[0118] Synthesis Example 4: Synthesis of [Compound 76] Synthesis Example 4-1: Synthesis of Intermediate D-1 JPEG2026009958000060.jpg29113<Intermediate B-1a><Intermediate A-1b> <Intermediate D-1>

[0119] Intermediate D-1 was obtained in the same manner as in Synthesis Example 1-1, except that Intermediate B-1a was used instead of Intermediate A-1a. (Yield: 77.4%)

[0120] Synthesis Example 4-2: Synthesis of Intermediate D-2 JPEG2026009958000061.jpg31128<Intermediate D-1> <Intermediate B-2a> <Intermediate D-2>

[0121] Intermediate D-2 was obtained in the same manner as in Synthesis Example 2-2, except that Intermediate D-1 was used instead of Intermediate B-1 (yield 75.1%).

[0122] Synthesis Example 4-3: Synthesis of Intermediate D-3 JPEG2026009958000062.jpg42130<Intermediate C-4> <Intermediate D-3a> <Intermediate D-3>

[0123] Intermediate D-3 was obtained in the same manner as in Synthesis Example 1-4, except that Intermediate C-4 was used instead of Intermediate A-3 and Intermediate D-3a was used instead of Intermediate A-4a. (Yield: 65.8%)

[0124] Synthesis Example 4-4: Synthesis of Intermediate D-4 JPEG2026009958000063.jpg41131<Intermediate D-2> <Intermediate D-3> <Intermediate D-4>

[0125] Intermediate D-4 was obtained in the same manner as in Synthesis Example 1-5, except that Intermediate D-2 was used instead of Intermediate A-2 and Intermediate D-3 was used instead of Intermediate A-4. (Yield: 64.9%)

[0126] Synthesis Example 4-5: Synthesis of [Compound 76] JPEG2026009958000064.jpg57125<Intermediate D-4> [Compound 76]

[0127] Compound 76 was obtained in the same manner as in Synthesis Example 1-6, except that Intermediate D-4 was used instead of Intermediate A-5. (Yield: 12.2%)

[0128] MS (MALDI-TOF): m / z 1129.52 [M + ]

[0129] Synthesis Example 5: Synthesis of [Compound 106] Synthesis Example 5-1: Synthesis of Intermediate E-1 JPEG2026009958000065.jpg33117<Intermediate E-1a><Intermediate E-1b> <Intermediate E-1>

[0130] Intermediate E-1 was obtained in the same manner as in Synthesis Example 1-1, except that Intermediate E-1a was used instead of Intermediate A-1a and Intermediate E-1b was used instead of Intermediate A-1b. (Yield: 73.1%)

[0131] Synthesis Example 5-2: Synthesis of Intermediate E-2 JPEG2026009958000066.jpg36123<Intermediate E-1> <Intermediate E-2a> <Intermediate E-2>

[0132] Intermediate E-2 was obtained in the same manner as in Synthesis Example 1-2, except that Intermediate E-1 was used instead of Intermediate A-1 and Intermediate E-2a was used instead of Intermediate A-2a. (Yield: 63.2%)

[0133] Synthesis Example 5-3: Synthesis of Intermediate E-3 JPEG2026009958000067.jpg42133<Intermediate C-4><Intermediate E-1b> <Intermediate E-3>

[0134] Intermediate E-3 was obtained in the same manner as in Synthesis Example 3-5, except that Intermediate E-1b was used instead of Intermediate A-4a. (Yield: 82.1%)

[0135] Synthesis Example 5-4: Synthesis of Intermediate E-4 JPEG2026009958000068.jpg41133<Intermediate E-2> <Intermediate E-3> <Intermediate E-4>

[0136] Intermediate E-4 was obtained in the same manner as in Synthesis Example 1-5, except that Intermediate E-2 was used instead of Intermediate A-2 and Intermediate E-3 was used instead of Intermediate A-4. (Yield: 75.3%)

[0137] Synthesis Example 5-5: Synthesis of [Compound 106] JPEG2026009958000069.jpg44123<Intermediate E-4> [Compound 106]

[0138] Compound 106 was obtained in the same manner as in Synthesis Example 1-6, except that Intermediate E-4 was used instead of Intermediate A-5. (Yield: 14.2%)

[0139] MS (MALDI-TOF): m / z 1092.47 [M + ]

[0140] Synthesis Example 6: Synthesis of [Compound 116] Synthesis Example 6-1: Synthesis of Intermediate F-1 JPEG2026009958000070.jpg34113<Intermediate E-1a> <Intermediate A-4a> <Intermediate F-1>

[0141] Intermediate F-1 was obtained in the same manner as in Synthesis Example 1-1, except that Intermediate E-1a was used instead of Intermediate A-1a and Intermediate A-4a was used instead of Intermediate A-1b. (Yield: 86.2%)

[0142] Synthesis Example 6-2: Synthesis of Intermediate F-2 JPEG2026009958000071.jpg36123<Intermediate F-1> <Intermediate B-2a> <Intermediate F-2>

[0143] Intermediate F-2 was obtained in the same manner as in Synthesis Example 1-2, except that Intermediate F-1 was used instead of Intermediate A-1 and Intermediate B-2a was used instead of Intermediate A-2a. (Yield: 80.3%)

[0144] Synthesis Example 6-3: Synthesis of Intermediate F-3 JPEG2026009958000072.jpg34125<Intermediate F-3a> <Intermediate A-1b> <Intermediate F-3>

[0145] Intermediate F-3 was obtained in the same manner as in Synthesis Example 1-1, except that Intermediate F-3a was used instead of Intermediate A-1a (yield 92%).

[0146] Synthesis Example 6-4: Synthesis of Intermediate F-4 JPEG2026009958000073.jpg35130<Intermediate F-3> <Intermediate A-3b> <Intermediate F-4>

[0147] Intermediate F-4 was obtained in the same manner as in Synthesis Example 1-3, except that Intermediate F-3 was used instead of Intermediate A-3a (yield: 45.2%).

[0148] Synthesis Example 6-5: Synthesis of Intermediate F-5 JPEG2026009958000074.jpg46128<Intermediate F-4> <Intermediate A-4a> <Intermediate F-5>

[0149] Intermediate F-5 was obtained in the same manner as in Synthesis Example 1-4, except that Intermediate F-4 was used instead of Intermediate A-3. (Yield: 84.4%)

[0150] Synthesis Example 6-6: Synthesis of Intermediate F-6 JPEG2026009958000075.jpg42130<Intermediate F-2> <Intermediate F-5> <Intermediate F-6>

[0151] Intermediate F-6 was obtained in the same manner as in Synthesis Example 1-5, except that Intermediate F-2 was used instead of Intermediate A-2 and Intermediate F-5 was used instead of Intermediate A-4. (Yield: 78.2%)

[0152] Synthesis Example 6-7: Synthesis of [Compound 116] JPEG2026009958000076.jpg55124<Intermediate F-6> [Compound 116]

[0153] Compound 116 was obtained in the same manner as in Synthesis Example 1-6, except that Intermediate F-6 was used instead of Intermediate A-5. (Yield: 13.2%)

[0154] MS (MALDI-TOF): m / z 1148.53 [M + ]

[0155] Synthesis Example 7: Synthesis of [Compound 151] Compound 151 was obtained in the same manner as in Synthesis Example 3, except that dibenzo[b,d]thiophene-4-amine was used instead of Intermediate A-4a in Synthesis Example 3-5. (Yield: 8.7%)

[0156] MS (MALDI-TOF): m / z 993.43 [M + ]

[0157] Synthesis Example 8: Synthesis of [Compound 154] Synthesis Example 8-1: Synthesis of Intermediate G-1 JPEG2026009958000077.jpg28112<Intermediate B-1a><Intermediate A-1b> <Intermediate G-1>

[0158] Intermediate G-1 was obtained in the same manner as in Synthesis Example 1-1, except that Intermediate B-1a was used instead of Intermediate A-1a (yield 78%).

[0159] Synthesis Example 8-2: Synthesis of Intermediate G-2 JPEG2026009958000078.jpg31128<Intermediate G-1> <Intermediate B-2a> <Intermediate G-2>

[0160] Intermediate G-2 was obtained in the same manner as in Synthesis Example 2-2, except that Intermediate G-1 was used instead of Intermediate B-1 (yield 72.1%).

[0161] Synthesis Example 8-3: Synthesis of Intermediate G-3 JPEG2026009958000079.jpg40128<Intermediate C-4> <Intermediate G-3a> <Intermediate G-3>

[0162] Intermediate G-3 was obtained in the same manner as in Synthesis Example 3-5, except that Intermediate G-3a was used instead of Intermediate A-4a. (Yield: 88.3%)

[0163] Synthesis Example 8-4: Synthesis of Intermediate G-4 JPEG2026009958000080.jpg34132<Intermediate G-2> <Intermediate G-3> <Intermediate G-4>

[0164] In the same manner as in Synthesis Example 1-5, Intermediate G-2 was used instead of Intermediate A-2, and Intermediate G-3 was used instead of Intermediate A-4, to obtain Intermediate G-4 (yield 68%).

[0165] Synthesis Example 8-5: Synthesis of [Compound 154] JPEG2026009958000081.jpg39118<Intermediate G-4> [Compound 154]

[0166] Compound 154 was obtained in the same manner as in Synthesis Example 1-6, except that Intermediate G-4 was used instead of Intermediate A-5. (Yield: 13%)

[0167] MS (MALDI-TOF): m / z 1069.46 [M + ]

[0168] Examples 1 to 7: Fabrication of organic light-emitting devices The ITO glass was patterned so that the light-emitting area was 2 mm × 2 mm, and then washed. The ITO glass was placed in a vacuum chamber, and the base pressure was adjusted to 1 × 10 -7 After adjusting the pressure to torr, a hole-injection layer (100 Å) was formed on the ITO using an electron acceptor of the following structural formula [Acceptor-1] and [Chemical Formula F] at a deposition ratio of [Acceptor-1]:[Chemical Formula F] = 3:97. A hole-transport layer (550 Å) was formed using [Chemical Formula F], followed by a 50 Å deposition of [Chemical Formula G] as an electron-blocking layer. An emitting layer (200 Å) was formed by mixing the host [BH1] described below with a compound of the present invention (2 wt%). Subsequently, a hole-blocking layer (50 Å) was formed using [Chemical Formula H], followed by a 1:1 deposition of [Chemical Formula E-1] and [Chemical Formula E-2] at 250 Å, followed by a 10 Å deposition of [Chemical Formula E-2] and Al (1000 Å) as an electron-injection layer, to produce an organic light-emitting device. The light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA.

[0169] JPEG2026009958000082.jpg51150 JPEG2026009958000083.jpg42153[BH1] JPEG2026009958000084.jpg3137

[0170] Comparative Examples 1-2 An organic light-emitting device was fabricated in the same manner as in Example 1, except that [BD1] and [BD2] were used instead of the compounds used in Example 1, and the light-emitting characteristics of the organic light-emitting device were measured at 0.4 mA. The structures of [BD1] and [BD2] are as follows.

[0171] JPEG2026009958000085.jpg47105

[0172] The voltage, external quantum efficiency, and lifetime of the organic light emitting devices manufactured in Examples 1 to 7 and Comparative Examples 1 and 2 were measured, and the results are shown in Table 1 below.

[0173] [Table 1]

[0174] As shown in Table 1, the organic light-emitting device employing the compound according to the present invention as a dopant compound in the light-emitting layer of the device has significantly improved life characteristics and excellent external quantum efficiency compared to the devices (Comparative Examples 1 and 2) employing compounds that are comparable to the characteristic structures of the compound according to the present invention, thereby realizing an organic light-emitting device with high efficiency and long life.

[0175] Experimental example: Measurement of the maximum peak wavelength of EL The maximum peak wavelengths of EL for [Compound 12], [Compound 73] and [Compound 151] were confirmed under the same conditions as in the previous example.

[0176] JPEG2026009958000087.jpg51113 JPEG2026009958000088.jpg48104

[0177] [Table 2]

[0178] As seen in Table 2, in the compound represented by Chemical Formula A-1 or Chemical Formula A-2 according to the present invention, the polycyclic compound in which Structural Formula 1 is substituted at the R6 position exhibits a blue-shift phenomenon in which the maximum EL peak wavelength shifts to a shorter wavelength compared to existing compounds, and a wavelength of 454 nm or less was measured. Therefore, when the compound according to the present invention is used as a dopant in the light-emitting layer of an organic light-emitting device, blue light emission with improved color purity can be achieved. [Industrial Applicability]

[0179] The polycyclic compound according to the present invention can be used to realize a highly efficient, long-life organic light-emitting device with significantly improved life characteristics and luminous efficiency, and can therefore be industrially usefully applied to lighting devices and various display devices such as flat display devices, flexible display devices, monochrome or white flat lighting devices, monochrome or white flexible lighting devices, vehicle display devices, and virtual or augmented reality display devices.

Claims

1. An organic light-emitting compound represented by the following chemical formula A-1 or A-2. (In the above chemical formula A-1 and chemical formula A-2, Q １ ~Q ３ are the same or different and are each independently selected from a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aromatic heterocycle having 2 to 50 carbon atoms, a substituted or unsubstituted polycyclic non-aromatic fused hydrocarbon ring having 6 to 50 carbon atoms, and a substituted or unsubstituted polycyclic non-aromatic fused heterocycle having 2 to 50 carbon atoms; Y １ ~Y ３ are the same or different from each other, and each independently represents N-R １ , C.R. ２ R ３ , O, S, Se and SiR ４ R ５ is one selected from The R １ ~R ５ are the same or different and each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted a substituted or unsubstituted polycyclic non-aromatic fused hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted polycyclic non-aromatic fused heterocycle having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a nitro group, a cyano group, and a halogen group; The R １ ~R ５ are the Q １ ~Q ３ can be further combined with any one of the rings to form an alicyclic or aromatic monocyclic or polycyclic ring, The R ２ and R ３ and R ４ and R ５ can each be further linked to each other to form an alicyclic or aromatic monocyclic or polycyclic ring; The Y ２ and Y ３ At least one of the following is N-R ６ and R ６ is represented by the following structural formula 1: [Structural formula 1] In the structural formula 1, X is O or S; R １１ ~R １８ are the same or different and each independently represent hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted polycyclic non-aromatic fused hydrocarbon ring having 6 to 50 carbon atoms, a substituted or any one selected from an unsubstituted polycyclic non-aromatic fused heterocycle having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, a substituted or unsubstituted aluminum group, a phosphoryl group, a hydroxy group, a selenium group, a tellurium group, a nitro group, a cyano group, and a halogen group; The R １１ ~R １８ Any one of the above Y ２ or Y ３ and R １１ ~R １８ may be linked to each other or to adjacent substituents to form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring may be substituted with one or more heteroatoms selected from N, S, and O.

2. The organic light-emitting compound according to claim 1, wherein the chemical formula A-1 or the chemical formula A-2 is represented by either one of the following chemical formula A-3 or chemical formula A-4. (In the chemical formula A-3 and the chemical formula A-4, Z is CR or N; R is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted polycyclic non-aromatic fused hydrocarbon ring having 6 to 50 carbon atoms, a substituted or unsubstituted polycyclic non-aromatic fused hydrocarbon ring having 2 ... a fused aromatic heterocycle, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted germanium group, a substituted or unsubstituted boron group, a substituted or unsubstituted aluminum group, a phosphoryl group, a hydroxy group, a selenium group, a tellurium group, a nitro group, a cyano group, and a halogen group (wherein the multiple Z's and R's are the same or different from one another); The plurality of R may be bonded to each other or to adjacent substituents to form an alicyclic or aromatic monocyclic or polycyclic ring, and carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring may be substituted with one or more heteroatoms selected from N, S, and O; Y １ ~Y ３ are the same as those defined in Chemical Formula A-1 and Chemical Formula A-2.

3. 2. The organic light-emitting compound according to claim 1, wherein the compound represented by the formula A-1 or A-2 is any one selected from the following compounds:

4. a first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode; 2. An organic light-emitting device, wherein the organic layer contains one or more organic light-emitting compounds represented by the chemical formula A-1 or A-2 according to claim 1.

5. the organic layer includes one or more layers selected from the group consisting of an electron injection layer, an electron transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, and an emitting layer; 5. The organic light-emitting device according to claim 4, wherein one or more of the layers contains the organic light-emitting compound represented by Chemical Formula A-1 or Chemical Formula A-2.

6. 6. The organic light-emitting device according to claim 5, wherein the light-emitting layer comprises a host and a dopant, and the organic light-emitting compound represented by the chemical formula A-1 or A-2 is a dopant in the light-emitting layer.

7. The organic light-emitting device according to claim 6 , wherein the host is an anthracene compound represented by the following chemical formula B: 【B】 (In the above chemical formula B, R ２１ ~R ２８ are the same or different and each independently represent one selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted amine group, a substituted or unsubstituted silyl group, a substituted or unsubstituted polycyclic non-aromatic fused heterocycle having 2 to 50 carbon atoms, a nitro group, a cyano group, and a halogen group; Ar １ and Ar ３ are the same or different and each independently represent a substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 30 carbon atoms, Ar ２ and Ar ４ are the same or different and each independently represent one selected from hydrogen, a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, and a substituted or unsubstituted polycyclic non-aromatic fused heterocycle having 2 to 50 carbon atoms; D ｎ is Ar of formula B １ ~Ar ４ This means that the hydrogen atoms in n is an integer from 0 to 30.

8. The organic light-emitting device according to claim 7 , wherein the anthracene compound represented by the chemical formula B is any one selected from the group consisting of the following compounds:

9. The organic light-emitting device according to claim 6, wherein the light-emitting layer containing the organic light-emitting compound represented by Chemical Formula A-1 or Chemical Formula A-2 has a maximum peak wavelength of EL (electroluminescence) of 454 nm or less.

10. The organic light emitting device according to claim 5 , wherein the one or more selected layers are formed by a vapor deposition process or a solution process.

11. 5. The organic light emitting device according to claim 4, wherein the organic light emitting device is used in any one selected from the group consisting of a flat display device, a flexible display device, a monochrome or white flat lighting device, a monochrome or white flexible lighting device, a vehicle display device, and a virtual or augmented reality display device.

Images